The Wingman's Heart
by Blockious
Summary: She was what he wanted, what his heart wanted. He had a crush on her, and he wanted to tell her he loved her. There's just one thing, he was her wingman to get other guys. Jaune Arc has a crush on Yang Xiao Long, but he must suppress these feelings just to help her, but how long before the truth comes out? High School AU!
1. Wingman

**So for some context before going into this story. This is one of those High school AU's, so Beacon is a highschool. I know the way huntsman training goes is attending combat school before going to a huntsman academy, but I'd rather have it at highschool. Faunus are still a thing too. Also I won't be including Jaune's sisters because I can't be damned to remember all 6 (since one sister was now shown in V6) made up names and personalities.**

**Thats all, ONTO THE STORY!**

* * *

Jaune Arc was a simple boy. He attended Beacon High School, and lived with his parents. He had friends, quite a few, and he had a crush, but that's for later.

He was walking into Beacons unusually large cafeteria and spotted his friends.

He had 7 friends.

Pyrrha Nikos, the all star athlete of the school.

Lie Ren, the silent one, but knows martial arts and meditation techniques.

Nora Valkyrie, the ginger who had unusual amounts of energy and strange abilities that no man, woman, and possibly God could fathom.

Ruby Rose, the girl two years younger than the bunch but was accepted at the same time due to her high grades... at the time.

Weiss Schnee, the prim and proper kind of girl, heiress of the Schnee Electric company.

Blake Belladonna, a cat faunus, and ex member of a group called the White Fang, leaving when the group turned to violence.

Last was Yang Xiao Long. Ruby's sister by father, but still treats Ruby's mother as her own and thinks of Ruby as her full sister.

Jaune was particularly more close to Ruby and Yang. Especially Yang. They lived in the same neighborhood, so they attended the same elementary school. Jaune always found himself hanging out with them. As for Yang, he was her wingman. There were times when Yang would go out on dates, or gain an interest in guys, and it was his job to assist her, either in getting the guy to go out with her, or just helping her decide what to wear on a date or what to do on said date. Sometimes when things go south he would be the she would vent to.

There was just one teeny tiny problem...

Jaune had a crush on Yang for a while.

He never told her because she would always have eyes on someone else. Plus, she was way out of his league.

She's strong, beautiful, funny (despite some puns), and just fun to be around. But he never done anything. And he always helped her with any crushes she had, no matter how much it pained him.

It was for her sake, so he would always do his best that things go right for her and her crush.

So that led him to his current situation, where he was sitting beside Yang in the table they shared. As they ate, Yang elbowed his side to get his attention. When he looked at her, she leaned over to him and whispered in his ear, "Meet me after school, I got something I need your help with." When she moved away Jaune nodded his head in confirmation.

Classes rolled by and at the end of the day he sat in the cafeteria again, alone this time, waiting for Yang.

He knew what this was about. It was common that she would privately ask him to meet up after school to discuss about her current interest.

Yang was an adventurous kind of girl, so it was often that she would get intrested in other guys.

"Except me that is..." Jaune mumbled to himself. He knew there wasn't a chance he could ever go out with her, he was just a plain guy, and most guys she was interested in had good looks, or a built body. So there was no way she would-

"Hey there gloomy blondie." He heard a familiar voice whisper into his ear from behind, interrupting his thoughts. He realized while he was busy thinking, he was growing a bit of a sad expression.

"H-hey Yang! So what did you want to talk about?"

"Oh you know, the usual." She said casually as she sat down beside him.

"Let me guess, another guy? Who's the poor sucker this time?" He teased.

"Oh shut up!" She laughed.

"If anything they would be lucky to be dating a gal like me" She said proudly.

_"Damn right"_ He thought to himself.

"Sure Yang, sure. Anyways, the guy in question is?"

"Viridis Nell." She said as she showed him a picture.

Green hair, good looking face, arms showed a bit of muscle.

"So what do you need my help for?" He asked.

"What do you think I should do?" She asked.

"Simple, talk to him, either befriend him and get to know him or ask him out tomorrow." He said, giving her his ideas.

"Hmm, I'll go with ask him out."

"Quick and easy, like usual." He chuckled.

"Of course!"

They got up and made their way home.

They didn't live far so they could simply walk to and from school.

"Hey Jaune?"

"Yes?"

"Is there anyone you're interested in?"

His heart skipped a beat. He wanted to answer that question honestly. He really did. But...

"No, why?" He didn't have the guts to, not while she was into someone else.

"Just asking, that's all." She said casually.

"Ah."

As they passed Yang's home, she waved at him before turning to go towards her home, though they were surprised to see Ruby waiting outside.

She said hi to Yang before going over to Jaune.

"Hey, wanna hang out?" She asked.

"Sure, why not." He replied.

The two waved goodbye to Yang and made their way to Jaune's house.

Yang and Ruby visited Jaune's house several times, though Ruby visited more than Yang.

"So, you and Yang met up after school huh?" She asked him.

"Yep."

"Let me guess, another interest?"

"Yep"

"Ughhhh, Jaune! Why don't you ever tell her how you feel?!" She exclaimed in confusion. She was the only person who knew of his crush in Yang.

"Don't you feel something for always helping her with guys, despite you liking her?"

"I do, but it's not my place to say when she isn't interested in me." He said.

"But it's not fair!"

"It's okay Ruby, that's just the way things are."

Ruby pouted at that. She wanted to help Jaune get together with Yang, but she knew what he was saying.

_"It really isn't fair, huh..."_

* * *

**There we go! First chapter! I had this idea in my mind for a while now, and so now it can come to life! Leave a review on what you think so far!**


	2. A Trip

The day came when Yang was to ask Viridis Nell out on a date. The plan was simple, she would simply go up to him and ask him out on a night of fun. Lunch came and it was time.

"You remember the plan, right?" Jaune asked Yang as they walked into the cafeteria.

"Of course I do! I'm just gonna make my way over to him and ask him if he wants to go out with me. Simple!"

"At least you remember, I know you sometimes have a bad memory." He said giving her a sideways glace.

"Oh please, name one time I-"

"You once forgot the passcode to your phone and you begged me for hours to help you unlock it." He said giving a deadpanned look.

Yang looked to the side, avoiding his glare. "W-well I-"

"You forgot your motorcycle needed a new tire and drove without changing it, resulting you in sliding and falling off your bike" He said moving closer to Yang's face.

She started leaning back. "That wasn't-"

"You once forgot that you were baking cookies and almost made CHARCOAL out of them!" He moved even closer.

She looked back at him, giving him a slight glare of her own. "Hey! That was-"

"You even forgot that we were trying to surprise Pyrrha last year on her birthday and spilled the beans that we were having a party for her." He said, giving his final point.

Yang just looked down at the floor in a defeated manner.

Jaune just sighed and patted her head, just don't forget this plan.

As they walked, Jaune noticed the boy in question was walking towards them, and so he hatched a plan of his own.

"Actually, forget the plan." He said, surprising Yang as she looked at him with a bit of confusion.

"Good luck!" He suddenly said as he put his leg in front of her, causing her to make contact with it as she took her next step, making her stumble forward as she tried to regain her balance.

She suddenly collided into someones chest, causing her to step back a bit.

"Whoa there, you okay?" She heard a male voice speak.

"Sorry... My friend just tried to trip me and..." As she looked up at the person she bumped into and realized it was Viridis Nell himself in front of her.

"Uhhhh..." She was a little shocked, but then she noticed Jaune walk past them, giving her a wink and a thumbs up as he walked away.

"That sneaky little bastard..." She mumbled to herself.

"What was that?" Viridis asked.

"Nothing!" She said quickly.

"Alright then." He said as he started walking away.

"Wait! I had something to ask you!" She said before he got any further.

"Oh?"

"You, me, let's hit a club tonight." She said nonchalantly.

"Are you asking me on a date?" He asked.

"What if I am?" She asked with a smirk.

"Then I say hell yeah!" He exclaimed with a grin.

"Excellent! Meet ya at this club tonight." She said as she showed him the location of said club.

"Got it! See you then." He said as he walked off.

Yang let out a sigh of content, then turned around to find the blonde idiot that tripped her in the first place.

Jaune walked away from the two after tripping Yang. He knew he had hell to pay for it, but just because he's helping his crush ask out another guy doesn't mean he cant mess with her in his own way.

He sat down in their usual spot, though no one else was there yet.

He looked over at the two as he saw Viridis walk away, but then having Yang call out for him.

_"There's no way he would turn her down, who could?"_ He thought to himself.

He turned away from the two and looked at his food.

How long has he done this? He wondered. It's been years since he helped her with other guys, though it wasn't until two years ago that he realized his feelings for her.

He doesn't exactly remember how it happened, he only recalls looking at her one day and seeing her in a new light.

As he was lost in his thoughts, he felt someone smack his head.

"That's for tripping me you idiot!" Yang said with a huff as she sat down beside him.

"So how did it go?" He asked, ignoring the insult.

"Got me a date VB!" She exclaimed.

Jaune groaned at the mention of her nickname for him, Vomit Boy, or VB for short.

"Why wont you let go of that nickname?" He asked her, annoyed.

"Because it's fun to tease you! Besides, you threw up on my shoes." She said.

"I was sick!" He exclaimed.

"New shoes Jaune!" She retorted.

He let out a sigh as he just put his head on his arms.

"Anyways, you're gonna have to help me later on deciding an outfit." She said as she patter his back, standing up.

"Why me? Why don't you ask Blake or Weiss, hell even Ruby!" He said, turning his head to look at her.

"Because you're a guy, duh! Who else is better to decide what outfit a guy would like than you?" He couldn't deny that. Not only was he a guy, he was a guy that was crushing on her, so all the more reason that he would know what would make a guy more interested, not that she would know about his crush.

"Fine..." He said, giving up.

"That's the spirit! Now I need me some food, be right back." She said, walking away to buy food for herself.

Jaune let out a sigh as he turned his head back into his arms.

"You got roped into helping her again?" He heard a familiar male voice speak.

He looked up to see the source being Ren, with Nora at his side.

"Yeah... Now I need to help her decide an outfit." He said.

"Don't worry Jauney! I'm sure it wont be bad!" Nora said.

"Nora, last time I was at her house for two hours, two!" He said with a slight annoyance.

"Well you agreed to help her already, so no going back." Ren said plainly.

"I know..." Jaune said, sounding slightly tired.

Yang came back with some food in her hands and the others finally arrived at the table.

Lunch went by fast and once Jaune finished his food, he stood up and started walking to throw out his trash. As he took his first steps, Yang extended a leg out and tripped Jaune, just as he did to her earlier.

He stumbled forward and ended up bumping into a girl.

"Sorry sorry!" He apologized, not seeing who he bumped into.

"No no! It's alright, you just lost your footing, that's all." The girl said.

He looked at the person and saw two bunny ears on her head.

"No, my friend tripped me, probably to get revenge on me" He said rubbing the back of his head in embarrassment.

"Oh, that's alright. I know the feeling of having my friends doing the same to me." She giggled at the idea of her friends tripping her just for revenge.

"Well, I still should apologize to you for bumping into you. Sorry...?" Jaune trailed off, indicating for a name.

"Oh! Velvet, Velvet Scarlatina." She said her name with a smile.

"Jaune Arc." He said, returning the smile as he gave out a hand for her to shake.

They shook hands and parted ways. As he finally threw out his garbage, he walked back over to the table and thumped the top of Yang's head.

"Ow! What was that for?!" Yang cried out.

"You already smacked me over the head for tripping you, now its my turn." He said with a glare.

"Oh shush, besides, you seem to hit it off with that girl you bumped into."

"Yang you made me look like an idiot." He deadpanned.

"So yourself?" She said with a wide grin.

They could hear a few in the group snort a bit at the quip.

Jaune flipped her off as her stared off into space.

As he got lost in his thoughts again, he remembered one thing.

_"Aw man, I'm probably gonna be stuck helping her for hours again."_ Jaune thought to himself.


	3. The Club

**Just a quick note here regarding a couple reviews that were left after chapter two. I have no intention of making Velvet Jaune's "girlfriend" whom he is to "date" to make Yang jealous, or of the sort. She is just a new friend for Jaune.**

**Also to address someone, I don't mean to have it seem like Yang is leading Jaune on. It's more of a simple case that Yang just has an interest in other guys, so Jaune doesn't make a move because, after all, when you ask someone out you also have to consider the other persons feelings, so he wont make a move while her heart is elsewhere. I actually had this experience where I wanted to ask someone out but they had a crush on someone else, but I still assisted them to the best of my ability on getting the guy.**

**That's all for now.**

* * *

_"Just how many times have I gone through this?"_ Jaune thought to himself as he let out an audible sigh as he sat in the living room in Ruby and Yang's house.

Ruby, who was sitting beside him, gave him a confused look.

"What's wrong?" She asked him.

"O-oh, nothing. I was just wondering how much longer until she finally decides on an outfit. Last time it took two hours, I don't want to deal with that again.

"Ah, gotcha. Too bad this is your problem, not mine." She said as she got up. She gave him a wink and stuck out her tongue at him as she made her way up the stairs to her room.

"Why you... One day, there will be hell to pay for these two." He grumbled to himself.

About 10 minutes pass and the sound of a door opening and closing could be heard, followed by the sound of footsteps making their way down the stairs. The source revealed itself to be Yang. She wore a white top with black sleeves and collar, as well as a black skirt and leggings. (Her outfit in V2 when she went to Junior's with Neptune.)

Jaune's jaw dropped as he saw her.

"So, whaddya think?" Yang asks, which snapped Jaune from his stupor.

"Y-you look amazing! It's definitely new, and it suits you. It's not as revealing as your usual outfit when you go out but it still has great appeal to it." He says, trying to think of the right words to say.

"Awww. You are such a sweet talker! It's a wonder how you haven't gotten a girl yourself VB." She says with a laugh as she lightly punches Jaune in the arm.

"Heh, yea, big mystery..." He said, lowering his voice just a little, but not much for her to notice.

"Anyways, if this is good enough, then I'll be off for my date!" Yang said as she walked towards the garage.

"Alright. I'll head home then." He said as he made for the door to leave. Just as he was about to pass Yang, she put out an arm, blocking the path.

'Not so fast Jaune! You're coming with me!" She says with a grin.

"Wait, what?!" He exclaimed, very confused.

"You heard me! You're coming with me to the club and you're gonna sit kinda off to the side, just in case I need help with something on this date. Plus, I wanna drink, so I need me a driver to get home."

Jaune let out a long sigh.

"I don't have a choice, do I?" He asked.

"Nope!" She smiled at him as she grabbed his sleeve and pulled him into the garage.

They seated on Bumblebee, Yang's signature motorcycle, and put on their helmets. Once they were outside and ready to properly leave, Jaune spoke up.

"Hey Yang?"

"Yeah?" She responded as she revved the bike.

"Can you please not drive to faAAAAAAAAAST" He screamed the last part as Yang immediately took off at a high speed, making Jaune cling onto her for dear life.

After a short drive, they made it

the the club where Viridis was to meet with Yang.

Jaune stepped off the bike with slight hesitation after nearly blacking out on the ride.

"Never do that again, please Yang." He said, sounding like he was going to be sick.

"Oh man up Jaune! And don't try to live up to your nickname "Vomit Boy" right now, alright?"

He nodded as he got his bearings and the two entered the club. He was surprised at how big and busy the place was.

"Let's sit at the bar. Oh, but I'll sit a few seats away from you so Viridis won't think anything of it." She said as she dragged him to the bar. While they were of age to drink, Jaune opted for non alcoholic drinks since he had to drive her home.

While they waited, he got hooked on Yang's favorite non alcoholic drink, strawberry sunrise, which Yang recommended to him. They communicated over text while they waited for Viridis to arrive.

Moments later, said boy walked into the bar and spotted the blonde waiting for him. He walked on over to her and ordered a drink for himself, and thus starting the date.

* * *

Jaune watched the two from his spot on the bar. The two talked and shared some laughs. They occasionally went to the floor to dance together, something that which he watched her intently. He let out a sigh as he watched Yang dance. They way her hair flows, almost seeming to reflect the light and making her hair bright like the sun, her smile which showed the excitement of dancing with Viridis.

As he let out the sigh, he heard a cup being placed down beside him, the bartender refilled it and noticed the young boy's slight frown.

"I see you've been watching that blondie over there with the kid with the green hair. I believe you two came in together. You two siblings or something?." He asked

"Oh no, I'm just a friend of hers, her wingman, here to assist her in anyway needed on this date, plus being her designated driver." He explained.

"Well that's a mighty frown for a wingman. What's your problem?" The bartender asked.

Jaune was hesitant to mention, but he thought why not since he had a feeling he wasn't getting out of this. Plus he needed a bit of an outlet.

"That blondie over there has been my friend for as long as I can remember. At some point I ended up gaining the role as her wingman ever since her first crush. After many years I ended up falling for her, but her heart is somewhere else. During the time that I helped her ever since, I never once stepped in her way when it came to getting the guy she wanted. It's just not my place to do so." He explained, taking a drink from his cup.

"Sounds like a rough time then. I wish you godspeed with this then. Not everyone is patient when it comes to matters of the heart. But sometimes its the patient ones who get rewarded the most." The bartender said, giving him words of encouragement.

"Thank you. I'm Jaune Arc." He introduced himself to the bartender who listened to his problems.

"Junior." The bartender gave his name, reaching out a hand for Jaune to shake.

They shook hands and Junior went back to attending to other customers.

Jaune noticed the couple coming back to the bar for more drinks.

Yang was starting to get a little tipsy but Viridis seem alright himself.

He watched as the two talked some more. But as the night grew older, he noticed Viridis say something to Yang which made her frown slightly. She shook her head as a response but he continued to persist.

She started to seem a little uncomfortable, so Jaune sighed as he got up.

He walked on over to the two and put a hand over his shoulder. "Hey, you seem to making her uncomfortable, why not lay off a bit?" He said.

Viridis stood up from his seat, being taller than Jaune he seemed a little more intimidating. The two stared at each other until they heard someone clear their throat.

They looked at the bar and saw Junior looking at them.

"No fighting in my club." He said sternly

"And I don't appreciate people making moves on my customers while they are intoxicated."

A couple of security guards came by to escort Viridis out of the building ,after paying for drinks.

They all left, leaving Jaune with a slightly cross Yang.

He sat down in the spot beside Yang and looked at her.

"You alright?" He asked her.

"Yeah... He was trying to ask me if we could find a hotel somewhere nearby, but I wasn't really for that. Though he kept persisting on the matter. Thank you, for stepping in." She said as she gave him a smile.

"No problem. Let's go home." She nodded at this.

The two paid for their drinks and exited the club and made their way to where Bumblebee was park. As they walked, they noticed how late it's gotten, as a result, how cold it was. A breeze flew by, making both of them shiver slightly.

"Man, fall's really coming around the corner huh?" Jaune said as he turned around to see Yang just slightly holding her arms from the cold.

He chuckled a little as he took off his hoodie. It's a good thing she told him to change before helping her with her outfit.

He handed her the hoodie. "Here, use this if you're cold."

Yang chuckled a little. "Well aren't you a cliche master? First stepping in to help a girl out, now giving her your sweater. Aren't you a bold one?" She said mockingly as she reached for it.

Just as she was about to take it, he reeled his arm back, as if retracting the offer.

"I was just doing that to be nice, but if you're gonna be like that then I guess no hoodie for you." He said, shrugging.

"So mean..." She pouted.

Jaune laughed as he reached out to give it to her again. "I'm just kidding. Take it."

She eyed it for a moment, waiting for him to retract it again, but after a moment, she quickly swiped the hoodie from his hand.

She put it on as Jaune got Bumblebee ready. He drove the bike on several occasions, Yang said it would come in handy since they always hung out. Yang got on the back and they put on their helmets before taking off. Jaune was a more careful driver, unlike Yang who was more into the thrill of high speeds.

They had a leisurely drive home, which allowed Yang to relax on the bike.

Once they got back to Yang's house, they parked the bike in the garage. Yang returned his hoodie to him and the two bid their goodbyes as Jaune went home.

Jaune thought about what happened at the club. It's a good thing he went with her otherwise things might've gone south.

He only shrugged as he cleared his thoughts as he reached his house. He was certainly going to get an ear full from his parents.


	4. When It Started

**So in order to establish a sense of time, they are all sophomores, second years.**

* * *

It was a regular weekend for Jaune. Ruby was over at his house, something common of the two as they shared so many similar interests in their dorky selves that they would always hangout, reading comics, watching their shows, playing games, whatever.

They were playing the latest edition of "Super Remnant Fighters", a game that Jaune mostly dominated at.

"Aghhhh... How are you so good at this Jaune?!" Ruby asked, exasperated.

"Practice Rubes, practice." Jaune responded with a smug grin on his face.

A moment passes before Rube spoke up.

"Hey Jaune?"

"Yes Rubes?"

"How did Yang's date go?"

He was surprised she asked, he figured she would've asked Yang herself that night or at least the day after.

"At first it was going well, she seemed to have had some fun. But then Viridis tried to make a move on her by getting her drunk, so I had to step in."

"That would explain why she seemed mad when she got home. How come you were there though?" She asked, a tad bit suspicious.

"Hold on! She wanted me to go with her so I could drive her home after her date." He explained.

"Oooohhhh, ouch... Getting dragged along on for a date your crush is going on just to drive her home, that must've really sucked." She said sympathetically.

"Yeah... It was disappointing to say the very least, but I am glad I was there to stop him from doing anything Yang didn't want to do." He said with a little bit of joy/

"Heck yeah! You're like her knight in shining armor!"

"Hahaha, maybe!"

"I bet if we lived in a world where we fought monsters and bad guys, you'd totally be a knight, sword and shield with armor!" Ruby imagined a world where such a thing occurred.

"I doubt I would be that cool Rubes." He said scratching the back of his neck.

"Maybe, but I guess we'll never know."

"Yeah."

The two started another match, and once again Jaune was beating Ruby at the game. Just as Jaune was about to finish her off again, she asked him another question.

"When did your crush on Yang start?" She asked casually, which threw him off guard and he missed the final attack, causing him to get hit by Ruby, and she finally wins for once.

"R-Ruby! That was cheating and you know it!" He exclaimed, slightly embarrassed, to which she responded with her sticking out her tongue at him.

"Maybe, but I am curious."

Letting out a sigh, he decides to just tell her.

"Remember when we went to Signal?"

"Yeah! When we were much younger you used to get bullied so much." She said, remembering those days.

"Yup..."

* * *

**Signal Academy, 4 Years Ago, 6th Grade**

A younger Jaune was walking around in the school's playground. He was simply minding his own business when someone put a hand on his shoulder. He turned around to see the top bully Cardin Winchester with his group consisting of: Russel Thrush, Dove Bronzewing, and Sky Lark.

"Hey there Jauney boy, we just got bored and having nothing to do, but we saw you wandering around by yourself, so we thought 'Why not have some fun with our good pal Jaune?'" Cardin said, with a menacing grin.

"Uhh... I think I'd like to refuse..." Jaune responded meekly.

"Too bad! You don't have a choice."

Cardin and Russel lifted Jaune up and carried him around a corner of the playground where no teacher could see them.

The tossed Jaune onto the ground against the wall, landing with a grunt.

"Now then, we thought of a nice game to play with you, it's called "Knockout". We're gonna take turns hitting you, and whoever deals the blow that knocks you out, wins! Sounds like fun right?" Jaune whimpered at the thought.

"Let's start!" Cardin immediately started with a punch to Jaune's gut.

The four bullies took turns attacking Jaune, and all he could do was lay there as they continued their onslaught.

Just as he felt like he was going to lose consciousness, he heard a familiar voice call out to them.

"HEY!" Shouted a female voice.

The four looked at the source while Jaune could barely move. His eyes were half closed so he couldn't see clearly either.

"LET HIM GO!" The voice shouted.

"Who do you think you are-" Cardin was cut off as the person took a dash and punched him square in the face, knocking him onto the floor.

In that moment when the fist connected with Cardin's face, Jaune could just barely make out the golden blonde hair that belonged to the person. The hair flowed and seemed to shine off the sunlight, making it seem to be ablaze.

"Anyone else want a piece?!" The voice shouted.

The others grabbed Cardin and ran off, leaving the two alone.

The person looked at Jaune and quickly changed expression from fear to worry.

"Jaune! Oh my God are you okay?!" She asked.

She helped Jaune sit up straight against the wall.

"Jaune started to get his bearings and soon recognized the lilac eyes that looked into his own with concern.

"Y-Yang! Was it you who saved me?" He asked.

"Of course! I noticed you weren't around and I searched all over the place until I saw them beating someone, I just can't believe it was you there. You had me worried there."

While Yang was explaining, Jaune just seemed affixed on Yang herself. He remembered seeing how her hair flowed and shined, and he was now starting to see her beauty. Especially those beautiful lilac eyes of hers that showed great concern for him, and the concern she would show for her friends. It wouldn't be until long after that he realized the feelings he developed for her.

Yang extended a hand out for him to grab to help him up.

"Come on! We need to get you patched up." She said, beaming a smile at him.

He took her hand and she lifted him up, and she assisted him to the nurses office to get his wounds bandaged up.

That was the start of his crush.

* * *

"Awww... Sounds like Yang was your knight in shining armor then." Ruby said with a giggle.

"Yeah, I guess so." Jaune said, slightly embarrassed.

"But wait! When did you start becoming her wingman?" Ruby asked.

"Well... That would be around our last year in elementary."

* * *

**Signal Academy, 2 Years Ago, 8th Grade**

Jaune was hanging out at Ruby and Yang's house. Ruby was out at a friends place, leaving Jaune and Yang together.

They were playing the version of "Super Remnant Fighters" That was out at the time.

"Jaune! You're clearly cheating! How else could you have won 5 times in a row?!" Yang complained as she lost, yet again.

"What can I say? I'm just better!" He said proudly.

"Yeah, too bad not in a real fight." She said smugly, as to crush his ego.

"Hey! There were four of them at the time, lay off!" He exclaimed.

"Hahaha, I'm just teasing you. Besides, I don't think you had anything to worry about since they left you alone since that day."

"Yeah, thanks for that. I'm glad they stopped bothering me."

"No problemo VB!" She said, dropping the nickname.

"Hey! I thought we moved past that!" He said embarrassed.

"Never have, never will!" She said smugly.

Jaune let out a sigh of defeat.

"Oh yeah! Jaune, I had something I wanted to ask of you."

"What is it?" He asked.

"Well, to be honest, it;s something I thought I could only ask of you for this." She said, slightly embarrassed.

'Wait a minute, is this what I think it is?' Jaune asked himself.

"You see... There's someone in our class that I've been interested in for a while now, and I wanted to ask them out."

'Oh my God it might be!' Jaune started to build up excitement.

"So... I was wondering."

'Yes...'

"If you..."

'Yes!'

"Would..."

'YES!'

"Help me out at asking them out!" She said finally.

'I DO- wait... WHAT?!' Jaune felt his excitement just leave him, as he turned slightly pale.

"I wanted some help, and since you're a guy, I thought you would be perfect for this!"

Jaune was devastated. Not only was this NOT a moment of confession of her having an interest in him, but rather an interest in someone else. And he was being recruited to help her get the guy she wanted.

By all means, Jaune wanted to reject her, deny it and ask her for her love to be towards him. But he didn't have the courage to. He didn't want to be selfish, so, he painfully accepted.

"O-of course!" He said, in a slightly sad tone.

"Oh thank you Jaune! You're the best!" She said as she gave him a bear hug.

Jaune felt crushed, both emotionally and literally. To this day he swore he heard a bone crack.

They started another round in their game, but Jaune was noticeably doing worse than before.

Yang picked up on this and noticed Jaune's gloomy face.

"Jaune? What's wrong?" She asked him.

"Huh? O-oh, nothing! I guess I'm not feeling too well right now, maybe I should head home now." He said as he got up, quickly grabbing his things and made for the door.

"Oh wait! I'll go with you." She said as she got up.

"It's fine!" He shouted, a bit louder and more forceful than he wanted.

He quickly opened and shut the door, leaving a confused Yang.

Jaune went home that day, with his heart slightly broken.

* * *

"Oh Jaune... That must've been a terrible day for you." Ruby said sympathetically.

"Yeah, it was horrible. Being told my crush has interests in someone else, and being asked to help her ask them out. It was devastating." Jaune said, feeling slightly sad at the memory.

Ruby moved to Jaune to give him a comforting hug.

"It's okay Jaune. Surely one day things will get better."

"Well... I certainly hope so..."


	5. Library

Jaune was sitting at a table in the school's library. He was doing some research for a project. As he tried his best to focus on the pages, he struggled very hard to understand what was on the pages.

He let out a sigh of frustration and just let go of the book, causing the poor entity of paper to fall backwards onto the table.

Jaune just put his head down in his arms. As he sat there, he was starting to think about the conversation he had with Ruby the other day.

'It's been years since I fell for Yang, and yet here I am, to this day still her wingman. I really want to tell her but, the timing... it's never right.'

As he mulled over his thoughts, someone spoke up behind him.

"Um... are you alright?"

Jaune turned around to see Velvet looking at him with curious eyes.

"Oh! Velvet, right?" Jaune said as he raised his head. She nodded her head, confirming his guess.

"Yeah, I'm alright, it's nothing big." He said.

"Are you sure? You seemed a bit frustrated for a moment, and then you seemed a bit sad." She said.

"Oh, I was just doing a bit of research for a project, I got a little frustrated at a few bits." He replied as he held up a book on history.

"Whats your project about?" She asked as she sat down beside him.

"I chose to cover a tragedy in history, one that left an impact either to a continent or world wide. Thing is though, I haven't decided on what I should cover."

"Well, what about the tragedy of Mountain Glenn?" She asked.

"What's that?"

"It happened almost half a century ago when Vale was still expanding. They decided to start building another city on a mountain, Mt. Glenn. They also converted the caverns into a tunnel to connect a rail system between Vale and the new city. It stood for a short time, housing millions. Unfortunately, a company called Merlot Industries was running experiments under the city, one that caused a major explosion. The city fell due to the explosion, and so the citizens fled to the tunnels to escape. But as they made their way to Vale, an earthquake occurred, caving both the way in and out, leaving the citizens trapped. With no escape, and no immediate help available to handle such a disaster, the tunnel became their tomb."

Once Velvet finally stopped telling the grim story of Mt. Glenn, she looked over to Jaune who was staring at her in awe.

"It's amazing that you know so much about history!" Jaune exclaimed.

"Now I know what I can do for my project! Thanks Velvet!"

"Oh, no problem! I'm glad I was able to help you." She smiled at him, grateful for being able to assist him. As the two talked a bit more, a familiar voice spoke up.

"Heya Jaune! What'cha doing here?" Jaune looked up to see Yang standing on the other side of the table.

"I was just working on the project Professor Ooblek assigned. Velvet here gave me a great idea on what to write about." Jaune explained.

"Ouuu, what's this? Jauney getting a bit of help from a girl? Don't tell me you've already found a girlfriend Jaune?" Yang teased.

"OF COURSE NOT!" Jaune blurted out a bit more forceful than he wanted.

Yang just raised a brow at the outburst.

"Are you okay Jaune?" Velvet asked with concern.

"Yeah, I'm fine." He said before looking at Yang.

"There isn't anything like that between us Yang, we just started getting acquainted with each other. That's all." Jaune explain.

"Gotcha, sorry about that you two, I'll leave you guys alone now, bye!" Yang said, turning around to leave the library.

Once she was out of earshot, Jaune just let out a sigh and put his head back on his arms again.

"What's wrong Jaune?" Velvet asked.

"Nothing, I just feel... tense." He replied.

"Does it have something to do with your outburst there?"

"..." He nodded slowly, not raising his head.

"Do... do you mind sharing with me, if you not then that's alright."

Jaune turned his head to look at Velvet and thought to himself for a moment.

He concluded Velvet seemed to be trustworthy.

"Alright, I'll tell you." He said with a sigh as he sat down properly.

He began telling her the same thing he told Ruby. He told her of his crush on Yang, how he developed it, and how he became her wingman.

"So you felt worried because Yang thought of us as a couple, when you secretly love her?" Velvet put together from earlier.

"Yep, I was worried Yang would think we were a couple and I would lose a chance with her."

"Honestly, I think it's kinda sweet that you put aside your feelings for Yang when you knew her heart belonged to another, but for so long? You should tell her one day, because I can't imagine going through something like that for so long."

"Thanks Velvet, I know I should, but everytime I think of doing it, I just clamp up and shut down."

"Hmmmm... I got it! There's the annual Beacon fall dance happening soon, you should ask her to be your date, before someone else does." Velvet suggested.

"Yeah, that's a great idea! Thank you!" He said gratefully.

"You're welcome." She smiled at him.

The two exited the library and went their own ways.

As he walked through the halls, Jaune saw a poster for the dance.

'Ask Yang to the dance huh? Easier said than done. It's true I should ask her but, what if she has someone else in mind?' Jaune kept thinking about this, unaware of Ruby, who hid behind a corner, who saw Jaune stare at the poster.

Once he was gone, she walked over to the poster and saw it was for the fall dance.

'Oh this will be perfect! I could get Jaune and Yang to go together! But how... Jaune might be to chicken to do it though... I need some milk and cookies to think about this...' Ruby thought as she walked towards the cafeteria.


	6. Ruby's Plan

**So somehow this hasn't gone through to people yet so I want to make this clear. I'm not gonna try to do the whole "Wimpy character becomes the coolest student ever" nor the "Protagonist dates another girl to make other girl jealous" cliche. I am NOT making Jaune seem like the thinks he isn't worthy of dating Yang, it's just a matter of Jaune putting aside his feelings to make Yang happy, even if the person she wanted to date isn't him, simple as that. We all on the same page now? GOOD!**

* * *

Ruby was sitting on her bed with a pencil and notepad, thinking of ways on how to get Jaune to ask Yang to the dance, and maybe finally ask her out. She was a bit frustrated, since she knew Jaune's timidness might stop him from ever doing so.

'Ughhh... Jaune... how is it that you've stayed silent for so long about this?! So many people would've cracked by now!' She thought to herself.

Growing bored, she fell backwards to lay down. She turned her head to the side and noticed a flyer for a new cafe that's opening nearby. She quickly scrambled to grab the flyer, nearly falling off her bed, but managed to keep her legs on her bed as she reached over to grab it.

Finally acquiring the paper, she quickly read it and decided this would be the perfect way to start.

"I AM A GENIUS!" Ruby exclaimed, not realizing that in her excitement, she pulled her legs away from her bed, causing her arms to finally give way, and she crashes into the floor.

"Ow..." Groaned the girl.

She got up and exited her room, making her way to the living room to where Yang was.

"Yaaaaaaaaang!"

"Yes Ruby?" Yang asked, craning her back to look at Ruby over the couch upside down.

"There's a cafe opening nearby, and I wanna check it out this weekend! Can you come with me?" She asked.

"Yeah sure, I got nothing going on."

"Thank you!" She exclaimed, running back to her room.

Once she entered, she scanned the room for her phone, finding it on her desk.

She quickly snatched the device and scrolled through her contacts before stopping on Jaune to call him.

The phone rings a few times before he picks up.

"Hello?"

"Hey Jaune!"

"Hey Rubes, how can I help ya?"

"A new cafe is opening nearby and I was hoping you could come with me this weekend, what'd ya think?"

"Hmmm, I think I should be free this weekend. Yeah, I'll go."

"Yes! I'll have to meet you there though, okay?"

"Alright."

"Okay, bye Jaune!"

"Bye!"

Once the phone call ended, she immediately jumped for joy, her plan was starting to take place.

"Ruby Rose, you are a genius." She said to herself, smugly.

Though in a short moment, she suddenly thought something to herself.

"Wait... why does this seem so... cliche?"

"Yaaaang! Come on!" Ruby cried out as she waited for Yang.

"I'm coming, no need to rush."

The two got on Bumblebee and made their way to the cafe.

They arrived at a cafe that had the sign "John's" at the front. Yang was also certainly surprised to see Jaune there waiting.

"Hey Vomit Boy!" Yang called out, which cause Jaune to physically flinch at that, while some turned their heads towards Yang, then Jaune.

He quickly walked over to the two, embarrassed.

"Yang could you please not call me that in public!" Jaune said annoyed, which Yang laughed at.

"No can do." She she said with a wide grin, which Jaune just sighed at.

"Whatever. So i'm guessing Ruby asked you to go with her here?" He asked.

"Yep. She seemed really interested in going so I thought why not take her. Didn't expect you to be here too."

"Ruby also asked me to come, though she said to meet her here, she never mentioned anything about you coming though." He said, sending a glare at Ruby, knowing she had something up her sleeve.

She only chuckled nervously as Jaune glared at her.

"W-well, since we're all here, why not enjoy it?" She asked, hoping to avoid Jaune pressing on the matter.

"Might as well." Yang said, shrugging as she walked inside.

Just as Ruby was about to follow, Jaune grabbed the back of her shirt, preventing her from escaping.

"Care to explain why Yang is with you?" Jaune asked, seeming slightly mad.

"C-cant I bring my sister along for some sisterly bonding?" She replied meekly.

"I don't think that's the only reason."

"FINE! I wanted to give you an opportunity to ask Yang to the fall dance, I think you should!"

Jaune sighed.

"Ruby, you should just let me ask her when I think I should." He said, to which Ruby looked down, slightly sad.

Letting out another sigh, he patted her on the head.

"It's alright Rubes, I know you were just trying to help. Come on, let's not keep Yang waiting." He moved his hand away and walked into the cafe, Ruby following behind.

Once they were inside, they spotted Yang sitting at a table, waiting for the other two.

"What took ya so long?" Yang asked.

"Oh, I just had to quickly ask Ruby something, that's all." Ruby flinched slightly at his response.

"Okay then. Well I got us this table and got some menus, so hurry up!"

The two sat down with Yang and they all went through the menu. The two blondes noticed that a certain girl was drooling at something in the menu.

Jaune leaned over to see what it was, and saw a strawberry shortcake that took the strawberry part of it to another level. Sitting back normally, Yang gave him a confused look, wondering what she was looking at. He merely smiled slightly and shrugged his shoulders.

Soon, a waitress shows up with a pencil and a notebook.

"Hello! My name's Velvet, are you ready to order?" Said the waitress, now revealed as Velvet.

The three turned their heads, surprised to see her here.

"Velvet! What a surprise! Are you working here?" Jaune asked.

"Yeah! This place opened recently so I took the job. The owner is really nice, and Russel is also here, but he's in the back." They were surprised to hear that Russel managed to land a job, even a decent one.

"Well that's good to hear. Anyways, yeah, I think we're good to order, right guys?" The two girls nodded in response.

Velvet took their orders and went off. She soon came back with a tray of items.

Jaune had a cup of coffee with an apple pie, Yang had coffee as well, but she opted for a chocolate cake, and Ruby, predictably ordered the strawberry shortcake with a glass of milk.

They all talked while they ate, which meant more of Jaune and Yang talked while Ruby enjoyed the cake that seemed to made by the hands of God with ingredients from his forbidden garden. The other two chuckled at Ruby as she ate her cake.

Once she had finished her cake, she finally joined in with the two, who were just starting up a debate on whether or not Jaune cheats at games.

"I do not cheat!" He exclaimed, throwing his hands in the air.

"You absolutely do! You beat us all the time! There has only been a few times where we won, and that was just by pure luck!" Yang said, pointing a finger accusingly at Jaune.

"It's not my fault that I'm good at the games, maybe you should play more so you can finally beat me." He said, crossing his arms.

The two girls shared a look before grinning at each other. Jaune definitely did not like the look the two had.

They suddenly jumped from their seats and started jabbing Jaune in the sides, which caused Jaune to squirm, both because it tickled, and hurt when they did that. This went on for quite a bit, others were giving the trio a look, but then quickly ignored them. They finally stopped when Velvet came with the bill, telling them to stop harassing the poor boy.

Jaune tried to pay for the two, but they profusely refused him to cover them, so they each paid for their respective orders.

Jaune and Yang stepped outside while Ruby went to the bathroom inside the cafe.

As the two waited, Jaune spoke up.

"Hey Yang?"

"Yeah?"

"Are you planning to go to the fall dance at Beacon?"

"Hmmm, maybe. I haven't fully decided since I don't have a date to go with. Maybe I'll go and just hangout with the others. What about you?" She asked.

"W-well I had it in mind to go, there IS someone I want to ask to be my date to it, but I'm not really certain on how to ask her." He said.

"Well, I think you should ask her, it can't go too bad, right?"

"You're right."

"So, when are ya gonna ask the poor girl." She joked at him.

"Maybe now." He answered, which confused Yang. He turned to face Yang and gave a serious, yet slightly nervous look.

"Yang, would you like to go to the dance with me?"

A second passed, then another, more came by as Yang was quite surprised that he asked her. Just as she opened her mouth, Ruby burst through the door

"Alright, let's go home!" Ruby quickly noticed the looks the two were giving her.

"Wait, what happened?" Ruby asked, oblivious.

Yang sighed as she just dragged Ruby to Bumblebee so they could head home.

Just as Jaune seemed to lose hope, Yang turned around and gave him a wink and a thumbs up.

The girls got on the bike and bid Jaune goodbye before taking off.

Once they were out of sight, Jaune just let out a breath he didn't know he was holding. Just as he was recovering from the initial panic he was having, the door of the cafe opened, and Velvet popped her head out.

"Did you ask her?" Jaune turned around and nodded at her, to which Velvet clapped her hands together in delight.

"That's great! One step at a time Jaune!" She said before slipping back into the cafe.

Jaune stared off in the direction Yang and Ruby went.

"I can't believe that worked!"

* * *

**So Jaune finally had the courage to ask Yang. One step closer to his goal now!**


	7. Preparing

To say Jaune was freaking out was an understatement. He managed to ask his crush to the dance and she accepted. It took every ounce of his strength to not just pass out when he asked Yang. Though he couldn't freak out too much, he needed to get ready for the dance. Didn't stop him though

Jaune was browsing through a store, looking for a suit to wear. He came with Ren, as he needed his male friend for support. It's not that he didn't like the girls, but when you're friend circle mostly consists of seven females and one male, it made it hard to have those moments that guys can have when they're together. Ren also had to get a suit as Nora asked (made) him to go with her.

"Jaune, I know this is a big deal to you, but you need to relax. We need to focus on finding us some suits." On the way to the store, Jaune explained to Ren the reason why he was freaking out so much.

"I know, but still! This is like the first step to what I've been wanting for years!" He exclaimed

"Yes, I get that, but that's no reason to make yourself look like a lunatic in front of everybody." Ren stated, making Jaune freeze up for a moment, before looking around to see a few people looking at them, but turning their heads away when he looked towards them. Jaune could only blush in embarrassment.

He then turned back to the wall of suits, where he considered the options.

He thought about matching with Yang, but he didn't know what she was wearing to the dance, so that crossed that away. He decided maybe a simple black suit would be suitable. Though he gave it more thought.

'It is a FALL dance, so maybe I should get something suitable for the season.' He thought to himself.

He walked around the store, examining the variety of suits, until one in particular caught his eye. It was a black suit, paired with a grey vest underneath, but that wasn't the thing that stuck out to him. No, it was the way the suit was outlined in red, perfect for the colors of fall. **(Just imagine his suit from Dance Dance Infiltration)** He grabbed the suit, as well as a white undershirt and a red bowtie to go with it and went to try it on. After some moments, he stepped out revealing the well fit suit that fitted him nicely.

Ren looked at Jaune before nodding. "Seems like a good choice for the theme." Ren ended up picking a similar suit as Jaune's, but with grey outlines instead of red **(Also from DDI) **but still having a red bowtie.

The two paid for their suits and exited the store.

"Thanks for coming with me Ren, it was nice to have someone to help me with this stress." Jaune said.

"No problem, if anything, it gave me a chance to hangout with another guy, plus some time alone from Nora was needed" Ren said, which the two laughed at the last comment.

...

Then they suddenly felt a chill run down their spines.

* * *

Somewhere across town, a ginger girl sneezed and looked into a direction.

She narrowed her eyes before muttering "I'll break your legs, just you wait..." The girl said.

"Nora!" Yang called for her.

"Coming~" The girl, now named Nora said as she skipped over to the group. Ruby, Weiss, Blake, Yang, Pyrrha and Nora were all out dress shopping.

"What were you doing?" Pyrrha asked.

"Oh nothing, I had a feeling someone was talking about me, but it was just. a feeling." Nora said.

"Uh huh... Well alright then, well don't get left behind, we all need a dress for the dance. Don't wanna show up in regular clothes do you?" Yang asked.

"It's okay, if anyone laughs, I'll break their legs!" Nora said menacingly, more than what the others are comfortable with, causing them all to give awkward chuckles.

"In any case, I know a shop down the street from here, they make quality dresses." Weiss said proudly.

True to her word, they arrived at a shop, it seemed a little bit too fancy on the outside, but on the inside it was more nicer to their liking.

They spent several hours looking for a dress. Ruby settled on a black and red dress that suited her hair colors. Pyrrha, a red dress that went all the way down to her feet, but left her arms exposed. Nora, a simple pink dress, she wasn't too fussy about these kind of things. Weiss ended up also getting a simpler dress, but white with a black lace to wear underneath. Blake got both her short dress and under lace black (**Just imagine their dresses from "Dance Dance Infiltration"**).

Yang was the last one searching for a dress. As she browsed, Pyrrha approached her.

"So... I hear you're going to the dance with Jaune." She said.

"Yep, he just asked me out of nowhere when Ruby and I were with Jaune. It did surprise me." Yang answered.

"Do you have any plans after the dance?" Pyrrha asked.

Yang shot a quick sideways glance towards Pyrrha. It wasn't a secret to her that Pyrrha had some infatuation with the blonde boy. So she could only imagine how she feels at this moment.

"Not at the moment, there's still a bit of time before the dance, maybe Ruby and I can play some games and watch movies afterwards, who knows" Yang said, shrugging.

"I see."

A moment of silence passed.

"Do you intend to date him?" Pyrrha asked, which got Yang to tense up for a moment.

"Not really, not that there's anything wrong with Jaune. Maybe if he offered I might consider it, nothing solid though." Yang answered honestly.

"What about that other boy? The one you asked out not too long ago? What happened to him?"

"He made the wrong moves, so I ended that before anything more could happen."

Another moment of silence.

"Just don't do anything bad to Jaune, he's a good guy." Pyrrha said, walking away.

Yang just looked at her as she walked back to the group.

Yang turned her attention back to the rack of dresses she was looking at.

"Me and Jaune eh? That's an interesting one..." Yang muttered to herself.

'There really isn't anything wrong with Jaune. He's a kind guy, always helping others, especially his friends, he can cook, bake, sing, play guitar. I guess really it's just his confidence that's lacking, always doubting himself. Though what I said is true. If Jaune asked, I might consider it.' Yang thought to herself.

As she was thinking, she spotted a dress that piqued her interest. She went to it to inspect it, and smiled.

"Perfect."

* * *

**Shneesus-Weiss**,** it's been forever and a half since I last updated this story. But finally a chapter! I know my descriptions on the dresses were quite lacking, being a male I don't know a lot about them, so I had to do a bit of research to figure out something. Never even stepped foot in a dress shop. Anyways that's all for today!**


End file.
